Director of Product, AI (Remote Canada or US)

Director of Product, AI

The Role

We're looking for a Director of Product who leads from the front. You'll own the roadmap, the execution, and the outcomes. You'll also run discovery calls with dealers, prototype solutions, and dive deep into integration problems when needed. This is a player‑coach role with a builder’s mindset. You’ll design the system that gets work done using AI agents and automation alongside your team to maximize output.

You’ll report directly to the VP, Strategy & Partnerships, manage a small product team, and work with a cross‑functional group spanning engineering, customer success, design, and commercial. Your success will be measured on product velocity and outcomes, not headcount. Traveling to meet customers face‑to‑face is expected.

What You’ll Own

Product roadmap & platform strategy – define and drive the roadmap across Toolbx’s core platform, ordering, payments, catalog, integrations, and AI capabilities. Translate market signals, dealer feedback, and internal data into a sequenced plan that balances near‑term wins with durable platform value.

Hands‑on execution – lead discovery, prototype solutions, and ship features from concept to launch. You’re not above digging into edge cases in a supported ERP or joining a dealer’s IT call. You also identify automatable parts of the product development cycle and build those systems.

AI product development – own the product surface for Toolbx’s AI‑powered ordering automation (AIOA). Take it from early‑stage to a core reason dealers choose Toolbx.

Integration & ecosystem depth – own the platform‑to‑ERP integration strategy across our dealer ecosystem. Decide where to build, partner, or hold the line.

Team leadership – manage and develop a team of 2‑3 PMs, provide clarity, remove blockers, and enable excellent work. Hire well, coach constantly, and raise the bar on craft without creating bureaucracy.

Cross‑functional alignment – partner closely with Engineering, Customer Success, Sales, and Design to drive execution and keep all perspectives aligned.

Product operations & AI workflows – design and maintain the operating system for product work. Build agent‑assisted workflows for feature request triage, competitive monitoring, status reporting, and roadmap communication. Accelerate engineering cycles by automating handoffs, specs, and coordination.

What We’re Looking For

• 8+ years in product management, with meaningful time in complex B2B SaaS or vertical software platforms
• 3+ years managing PMs, having grown people, not just shipped features
• A track record of owning outcomes, not just outputs, with measurable impact
• Hands‑on AI product development experience; knowledge of real versus hype and ability to ship AI features that earn user trust
• Experience building AI‑assisted workflows for your own team, using agents, automation, or AI tooling to multiply output
• Integration fluency; experience with ERP, payments, or similar complex ecosystems and ability to scope without delivery blowups
• Strong discovery instincts; frequent customer engagement reflected in your roadmap
• Exceptional written communication; clear specs, traceable reasoning, and effective executive updates
• Bias for action; able to make decisions with imperfect information and own results
• Systems thinking; view the product org as workflows to design and optimize, not just a team to manage
• Flexibility to travel regularly to meet customers at their locations

Nice to Have

• Familiarity with LBM or distribution industry language
• Mobile‑first product experience, as many customers order from job sites
• Vertical SaaS or industry cloud background, built for buyers transitioning from spreadsheets and phone calls
• Early‑stage product leadership experience, building processes that help without slowing progress
• Experience at an AI‑transformed company, navigating the shift to AI‑native product development